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• W1548786064 endingPage "2669" @default.
• W1548786064 startingPage "2651" @default.
• W1548786064 abstract "Phenylhaloacetylenes are triphilic towards methoxide ion in methanol. With phenylchloroacetylene (1′), methoxide attacks ∼0·2% on chlorine, ∼99% on carbon 1, and ∼1% on carbon 2; with phenylbromoacetylene (1), methoxide attacks ∼5% on bromine, ∼83% on carbon 1, and ∼11% on carbon 2. The first detectable products, phenylacetylene, phenylmethoxyacetylene (2), (E)-β-bromo-β-methoxy- styrene, and (Z)-β-bromo-α-methoxystyrene lie on discrete mechanistic paths and are not interconvertible under the reaction conditions. Comparable amounts of alkynyl and alkenyl ethers are formed by attack on carbon 1. The element effects for attack on halogen, K(Cl)/k(Br) ⋍ 0·4, and on carbon 1, k(Cl)/L(Br) ⋍ 1·6 are consistent with the notion of independent competing processes. Phenylmethoxyacetylene is a short- lived transient; its formation and decay (with methoxide) rate constants at 78° arc k1′2 (Cl) 0·6 × 10−4 * or k12 (Br) 0·5 × 10−4 and Kj 1·7 × 10−3 M−1 sec−1. Previously, the intermediacy of alkoxyacetylenes under analogous conditions has only been surmised. In the course of this work, five of the six bromomethoxystyrenes were prepared and some of their distinctive chemistries, as well as those of the corresponding carbonyl compounds, were worked out (eq 2–4)." @default.
• W1548786064 created "2016-06-24" @default.
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• W1548786064 date "1971-01-01" @default.
• W1548786064 modified "2023-09-23" @default.
• W1548786064 title "Nucleophilic substitution at an acetylenic carbon" @default.
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• W1548786064 doi "https://doi.org/10.1016/s0040-4020(01)98055-x" @default.
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